This invention relates to energetic organic compounds. In one aspect, this invention relates to gem-dinitro precursor alcohols. In another aspect, it relates to azidodinitro compounds. In a further aspect, it relates to methods for preparing these compounds.
Energetic organic compounds have a long history of use in explosives and propellants. Examples have included polynitroaromatic compounds such as 2,4,6-trinitrotoluene (TNT); cyclic nitramines such as 1,3,5-trinitrazacyclohexane (RDX) and 1,3,5,7,- tetranitrazacyclooctane (HMX); and nitrate esters such as nitrocellulose (NC) and nitroglycerin (NG). Despite some shortcomings in terms of their thermal stability and sensitivity, these materials have seen heavy use during the past century.
More recently, considerable attention has been paid to various polynitro aliphatic compounds. Compounds, such as bis(2,2-dinitropropyl) formal/acetal (BDPNF-A) and bis(2,2,2-fluoridinitroethyl) formal (FEFO), have found widespread use as energetic plasticizers in modern explosive and propellant formulations.
Yet another promising class of compounds is the group of azido and azidonitro aliphatic compounds. Despite their well deserved reputation as sensitive materials, organic azides are potentially useful ingredients in energetic formulations because the azido group contributes 80 to 90 kcal/mol, while not detracting from the O/C ratio of the molecule. Incorporating both azido and polynitro functionalities in the same molecule generally has been accomplished by joining individual polynitroalkyl and azidoalkyl moieties via a non-energetic linkage. Examples include azidoalkyl esters of polynitroacids such as 1,3-diazido-2-propyl 4',4',4'-trinitrobutyrate (DAPT) and azide-terminated nitramines such as 1,7-diazido-2,4,6-trinitrazeheptane (DATH) and 1,5-diazido-3-nitrazapentene (DANPE). A more compact combination of these two functionalities would be the use of the azidodinitromethyl group in place of trinitromethyl and fluorodinitromethyl groups, which have been incorporated previously in propellant ingredients.
It is an object of the present invention to provide novel azidodinitro compounds.
It is another object of this invention to provide a method for preparing novel azidodinitro compounds.
It is yet another object of this invention to provide novel gem-dinitro alcohols.
It is a further object of this invention to provide a method for preparing gem-dinitro alcohols.
Other objects, aspects and advantages of the present invention will be readily apparent to those skilled in the art from a reading of the following detailed disclosure.